TY - JOUR
T1 - Triaryl Carbenium Ion Pair Mediated Electrocatalytic Benzylic C−H Oxygenation in Air
AU - Zhang, Zhenguo
AU - Lv, Yongheng
AU - Ji, Liang
AU - Chen, Peng
AU - Han, Shuyan
AU - Zhu, Yufei
AU - Li, Lanyang
AU - Jia, Zhenhua
AU - Loh, Teck Peng
N1 - Publisher Copyright:
© 2024 Wiley-VCH GmbH.
PY - 2024/7/8
Y1 - 2024/7/8
N2 - The selective oxidation of benzylic C−H bonds is a pivotal transformation in organic synthesis. Undoubtedly, achieving efficient and highly selective aerobic oxidation of methylarenes to benzaldehydes has been highly challenging due to the propensity of benzaldehyde to undergo overoxidation under typical aerobic conditions. Herein, we propose an innovative approach to address this issue by leveraging electrocatalytic processes, facilitated by ion-pair mediators [Ph3C]+[B(C6F5)4]−. By harnessing the power of electrochemistry, we successfully demonstrated the effectiveness of our strategy, which enables the selective oxidation of benzylic C−H bonds in benzylic molecules and toluene derivatives. Notably, our approach exhibited high efficiency, excellent selectivity, and compatibility with various functional groups, underscoring the broad applicability of our methodology.
AB - The selective oxidation of benzylic C−H bonds is a pivotal transformation in organic synthesis. Undoubtedly, achieving efficient and highly selective aerobic oxidation of methylarenes to benzaldehydes has been highly challenging due to the propensity of benzaldehyde to undergo overoxidation under typical aerobic conditions. Herein, we propose an innovative approach to address this issue by leveraging electrocatalytic processes, facilitated by ion-pair mediators [Ph3C]+[B(C6F5)4]−. By harnessing the power of electrochemistry, we successfully demonstrated the effectiveness of our strategy, which enables the selective oxidation of benzylic C−H bonds in benzylic molecules and toluene derivatives. Notably, our approach exhibited high efficiency, excellent selectivity, and compatibility with various functional groups, underscoring the broad applicability of our methodology.
KW - benzylic C−H oxygenation
KW - electrocatalysis
KW - ion pair
KW - triaryl carbenium
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UR - http://www.scopus.com/inward/citedby.url?scp=85194968731&partnerID=8YFLogxK
U2 - 10.1002/anie.202406588
DO - 10.1002/anie.202406588
M3 - Article
C2 - 38664822
AN - SCOPUS:85194968731
SN - 1433-7851
VL - 63
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 28
M1 - e202406588
ER -